The deepening crisis in Iraq may be shaping up to be President Obama's biggest test—and not only because of the risk of the country fracturing along sectarian lines and the potential for the rise of a new jihadist terror state.

Few, if any, challenges faced by this White House have cut so forcefully against the president's own personal and political instincts. If Obama is to help bring stability to the region, experts say, then he will have to do the kinds of things he has long resisted: Get his hands dirty, go it alone, admit his mistakes, and dig in for the long haul.

This is a president, after all, who has made winding down conflicts—not escalating them—the hallmark of his foreign policy. And in other arenas—Syria, Ukraine, Iran—to name just three, he has shown a preference for a deliberative approach, for soft power and sweet reason. Politically, he has liked to operate with public opinion on his side; indeed, in everything from health care to immigration to gay rights, White House aides have often used shifting public attitudes as justification for the president's actions. And it goes without saying that this is a White House that rarely concedes its missteps.

Iraq scrambles all of that. The electorate is dead set against further U.S. involvement. The forceful march of ISIS, as well as increasing Iranian influence in the region, cries out for urgent action. Allies in the fight willing to commit resources are scarce. And nothing about the theater suggests the kind of surgical and consensual approach that worked for Obama in, say, Libya. Obama is like an NFL coach whose playbook no longer works.

Because of the president's hands-off style, critics worry that the White House won't engage on the level needed to stave off the defeat of the Iraqi government. "The idea that he's now prepared to acknowledge the collapse of one of the foundational pillars of his foreign policy, and invest his personal prestige and political capital in the difficult, messy, and risky business of stabilizing Iraq's dysfunctional politics and reversing the emergence of an al-Qaida proto-state in Mesopotamia is almost preposterous," said John Hannah, a senior fellow at the Foundation for the Defense of Democracies. "I hope he proves me wrong."

Hannah was a national security adviser to then-Vice President Dick Cheney, so his skepticism comes naturally, as it does for House Speaker John Boehner, who, his aides say, doubts the president's commitment on Iraq. But even former members of the Obama administration see the White House as just beginning to realize the enormity of the challenge on its hands—and that it's one that, even after all his years in office, could shape the president's legacy.

"I think the president is finally grasping that this is the problem that he will be judged by," said Douglas Ollivant, former Iraq director on the National Security Council under both Obama and George W. Bush.

The war in Afghanistan—and the "surge" there that Obama endorsed before his decision to exit the country—was premised on the idea of denying a safe haven for al-Qaida. Last week, in announcing he was sending 300 U.S. military advisers to Iraq, Obama declared that it was in America's best interests to prevent a similar haven for terrorists from developing in the borderlands between Syria and Iraq. But Ollivant and others say that haven already exists—and is a burgeoning threat to the rest of the Middle East, especially Jordan and Lebanon. "I call it Somalia without a coastline," Ollivant said.

If Obama were to leave office with that kind of threat intact, all of his efforts to battle terrorism worldwide could pale in comparison. Indeed, even if the administration succeeds in its long-shot bid to persuade Iraqi Prime Minister Nouri al-Malaki to form a more inclusive government, an immediate question that will face Obama will be whether to help that new regime push ISIS back out of Iraq, something that experts say Iraqi security forces cannot do on its own and something on which it may look to Iran for help instead.

Retired Gen. David Petreaus, the former allied commander in Iraq, and others have warned about the risks of the U.S. appearing to take sides in a Sunni-Shia conflict—which means that it may become critical for Sunni moderates to be persuaded to side with the Iraqi government, and not the jihadist insurgency, in a bid to at least defuse the threat if not directly combat it. Here, too, the United States can play a role that Obama may find uncomfortable, analysts say.

"There's dirty, on-the-ground work to be done," said Kimberly Kagan, president of the Institute for the Study of War, which has been tracking the movements of ISIS across Iraq. "This is a classic mission for special operators or other elements of the U.S. government"—by which she meant intelligence agents.

"This is the hard stuff. This is totally dirty stuff. You have to be out there with the tribes," Kagan said, adding that those American forces would have to be protected by a larger unit than Obama has committed. "You have to have freedom of movement, which requires a heavier footprint. I don't see a lot of willingness to do that."

Beyond halting the advance of ISIS toward Baghdad, Hannah and Ollivant say Obama will need to be prepared to utilize U.S. airpower, including drones, to mount attacks within the territory controlled by ISIS both in Iran and Syria to knock out training camps and command centers, provocative actions that Obama has so far resisted even as the terrorism group has swelled in manpower and resources. Hannah, in addition, says Obama may have to reconsider its diplomatic position toward Iraqi Kurds in order to secure their support—another issue on which the White House has sent conflicting signals.

There are, however, indications that the administration is tossing its playbook, rethinking its approach, and beginning to see the problems in Iraq and Syria as linked. Obama on Thursday called on Congress to approve $500 million to train moderate rebels in Syria. "What they really ought to be doing is looking at this problem in a broader dimension in Iraq and Syria," said Frederic Hof, who was Obama's special adviser on Syria and is now with the Atlantic Council. "Fending off attacks [in Iraq] is not enough."

Hof, too, mentioned the kind of dirty work that needs to be done by Obama in Syria—to try to "very, very carefully" focus on the thousands of defectors and deserters from the Syrian army to put together a national resistance force to battle ISIL and move toward regime change in that country. ISIS could then conceivably be pinned down between Damascus and Baghdad.

But, he cautioned, "this is not something that's going to be accomplished in the next 20 minutes."

And that's what lies at the heart of the challenge facing the president. It's not going to be quick. It's going to be dirty. The public doesn't want him to be the one to go in and clean up the mess. There's every political reason to sit tight and let events play out without him. It's possible that Obama has never been in a tougher spot—and what he does in the next few weeks and months will say much about his presidency.

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